New Tech Founder Spotlight: Rebekah Bastian, CEO and Co-Founder, OwnTrail

Each week in the New Tech Newsletter we feature a Spotlight Q&A with founders, angels, New Tech alumni presenters, and other people or companies in our community we believe you’d like to learn about. Reach out if you’d like to recommend a startup, founder, angel, accelerator, or New Tech alumni presenter for us to spotlight for the PNW tech community!

In this week’s spotlight we caught up with Rebekah Bastian, CEO and Co-Founder of OwnTrail


Why do you do what you do for a living?
I’m building a startup that is basically solving the most important problem in human existence: how to live a fulfilling and meaningful life. OwnTrail lets people visualize where they’ve been and where they want to go in life, and helps them make that vision a reality. I feel like everything I’ve done and learned up to this point has brought me to this work. 

Why did you start your company?
I was at Zillow for 15 years before starting OwnTrail, and grew in my career there to vice president of product and then vice president of community & culture. People would ask me how I got to where I was, believing that there was some “right” path for them to follow, that they needed to know where they were going and how they’d get there. They were afraid to get it wrong. My desire to shout “there is no right path” led me to writing an award-winning book, Blaze Your Own Trail, which explores different life paths in a choose your own adventure format. And that led to OwnTrail. I started OwnTrail recognizing the importance of owning our journeys in a way that’s true to us, and the importance of seeing what other people’s journeys really look like. From there, we’ve built out a community and toolset to help people make progress towards where they really want to go.

What is one of the greatest lessons you’ve learned from being a founder/CEO?
On a positive note, I’ve learned about the lives of so many incredible people. There are thousands of trails on OwnTrail, and each one is so unique and inspiring. And we see folks making huge, brave, pivotal changes in their lives every day thanks to the support they find on OwnTrail, which is just incredible to be part of.
I’ve also learned that the venture capital ecosystem is even more biased and inequitable that I had realized. Sure, we all see the numbers, about women receiving 2% of venture funding and Black founders receiving <1%. But it’s not until you’re out there, raising and talking candidly with other founders, that you realize just how (intentionally) broken it is. I’ve been lucky to find an amazing, diverse set of investors that believe in us, but it’s taken hard work and thick skin to get there.
What is the one piece of advice you would share today with your younger self before you started your company?
I tend to not want to give advice to my younger self, since every mistake and failure has led me to where I am now. Kind of butterfly effect thinking 🙂 But I’ll say this to aspiring entrepreneurs: be incredibly intentional about who you bring on this journey with you. Your team, advisors, investors and the communities you’re in – they make all the difference, not just in whether or not your venture is successful, but in the experience you have along the way. If someone is not the right person at the right time for what you’re building, don’t hesitate to make the necessary changes so that you can create space for the people that are.

What is something interesting and unexpected that people would be surprised to learn about you?
I’m not sure about unexpected, since I’m a pretty open book! But perhaps interesting is that I love to fill my life with a multitude of creative outlets, and being an entrepreneur hasn’t stopped that. I prioritize time to create art, collaborate on Web3 projects, write, practice aerial, and build communities. And of course being with my family – I’m a mom of two fascinating boys. I think there’s a misconception that being a founder means being single-minded, but I find that all the facets of my life complement and enhance each other.
Reach out if you’d like to recommend a startup, founder, angel, accelerator, or New Tech alumni presenter for us to spotlight for the PNW tech community!
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